Holli met Ted in MacLaren's where she gives him her number. Unbeknownst to the real Holli, Barney switches her number in Ted's phone to the number of his work cellphone, leading to Ted texting Barney and Marshall thinking it was Holli. Eventually, Robin told Ted the truth and he obtained her real number. When Holli first appeared it was thought her name was "Holly" but then Ted revealed her name was "Holli". This is a reference to Barney's theory that girls whose names end in "ly" are "always dirty", while girls whose names end in "i", instead of "y", are "like roller-coasters; you have to wait in a long line, but once you get up there, you've just got to hold on for dear life, and hope you don't drop your keys".

They went on one date but Holli ended up doing everything that Barney and Marshall pointed out that Ted did in his "too soon" texting.